


Who's Your Date?

by Cpdfan231



Category: Chicago PD (TV)
Language: English
Status: Completed
Published: 2020-12-25
Updated: 2020-12-25
Packaged: 2021-03-11 00:29:10
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,317
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28306074
Author URL: https://archiveofourown.org/users/Cpdfan231/pseuds/Cpdfan231
Summary: This was for secret santa on Tumblr.Trudy organizes the guest list for the 21st District Christmas Party.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 2
Kudos: 58





	Who's Your Date?

It was a cold and windy morning like normal in Chicago, Trudy was working on some paperwork, when Jay walked into the district.

“Hey, Detective Chuckles come over here”. Jay sighed, he had not even had a cup of coffee to deal with whatever Trudy was going to ask of him.

“Yes, Sarge what can I help you with?” He said while trying to smile, but it didn’t quite reach.”

“Chuckles, you could put a little more effort into that smile, eh?” Trudy smirked

“Sorry, Sarge. I need some of this coffee.” He nodded his head in the direction of the two coffees in his hands.

“Don’t we all chuckles, don’t we all…” she mumbled looking at her empty coffee mug.

“So, what did you need, Sarge? I’m going to be late here in about five minutes.” Looking at his watch.

“I have not gotten your rsvp yet for the upcoming 21st District Holiday party. I need to know if you were planning on bringing a plus one.” She kept a straight face staring at him.

“Sarge, have I ever brought a plus one?” Looking super confused at the question.

“Chuckles, I don't keep track of your love life or lack of one, I guess.” Jay rolled his eyes, “Thanks for the reminder.”

“Fine, we can put this conversation on the back burner for now. But...it’s going to cost you.” Looking at the extra coffee he had in his hands. He sighed and looked down at it.

“Trudy, it was always meant for you, here you go.” He handed her the cup of coffee and headed up the stairs to join Intelligence.

Once, he got to his desk. He looked over and saw Hailey looking at him. She mouthed to him, “You’re late.” and Jay just whispered back looking annoyed, “You can thank, Trudy for that. Also, for your lack of coffee.” Hailey quirked her eyebrow and asked, “Do I want to know?”

“Nope. What did I miss?” Jay asked

We got a case and Sarge wants us to do some canvassing, “You ready to head out?”

“Sure.” Jay grabbed his coat and keys and they headed to his truck.

Hailey walked past Trudy's desk, staring at her coffee in Trudy’s hands. Trudy noticed and smirked and pointed the coffee in her direction. “Hey Upton, you should have told your partner to bring you one. It’s like heaven in a cup.” Jay saw Hailey about to react, when he pulled her down the stairs out of the precinct. He whispered in her ear, “I promise next stop is the coffee shop, before we canvas. Let’s go.”

* * *

Back from canvassing, Jay and Hailey walked into the district and Trudy called out to Hailey, “Upton, can you come here for a second?” Hailey looked at Jay confused, “Hm.. I guess it's your turn.”

“Wait, my turn for what? She turned to look at Jay, but he had already bolted up the stairs to Intelligence. She turned to face Trudy, smiled, and slowly made her way to her.

“Sarge, what can I do for you?”

“Well, someone must have stopped for coffee. I see you're in a better mood. You RSVPed for the Christmas party, but I did not see a plus one on it. I just wanted to make sure that wasn’t a mistake.” Hailey looked shocked at the question, “Um, nope. I did not forget to add a plus one. Also, my coffee was hijacked by a desk Sergeant”

“Really, who? Because I know you are not talking about me. Also, you know I have a nephew about your age. I could ask him.” Hailey was trying to keep her emotions in check throughout the conversation. “Really, I appreciate the offer. But, I’m good.”

“If you say so, well let me know if you change your mind. He’s got just as good of dance moves as myself. You definitely would not be disappointed” Trudy responded, raising her eyebrows up and down.

Hailey tries not to laugh, but it slips out a little bit. “Upton, what’s so funny?” Trudy just stared at her wanting a serious answer.

“Oh, sorry nothing. I was thinking back to when Kim and Adam started dancing on the bar at last year's party.” Hailey really hoped that Trudy would buy it and make her escape for the stairs.

“Nice try, Upton. Don’t ask for my help next time.” Hailey was about to respond back, "But, Sarge…" Trudy just kept blankly staring at her. She quickly pulled her cell phone out, “Oh, text from Jay, sorry Sarge, they need me upstairs.” She retreated to the stairs and headed up.

Trudy called after her, “Upton! I didn’t hear that phone go off.” But Hailey was long gone.

* * *

Hailey walked back up to Intelligence and headed to her desk and sat down. Jay was about to ask her how that conversation went when Kim walked up to Hailey.

“Hey, Hailey. Got a second? Coffee?” Hailey shot Jay a quick smile and followed Kim to the break room. Once inside, Kim shut the door.

Hailey looked confusedly at Kim. Kim went over the coffee maker to grab herself a cup. “So, are you excited for the Christmas party coming up?”

“Um, yeah I guess.” Hailey answered not sure where this conversation was going after the one downstairs. She had her guard up.

“I’m excited to be going this year with Adam. At least if we end up dancing on the bar together this year, it won’t be so weird… They both started to laugh thinking back to that scenario, where Adam ended up shirtless on that bar top.

“Do you have a date for the party?” Kim asked curiously while sipping her cup of coffee.

Hailey was in the middle of drinking her coffee when Kim asked and almost choked on it.

“Sorry, are you and Trudy working together on something here?” Kim looked at her shocked, not expecting that answer. “Um...no? I was just trying to have some girl talk, but if it's a touchy subject we don’t have to talk about it.” Hailey sighed, “No, of course not. Let’s just say it was just brought up by Trudy downstairs. Kim chuckled and completely could picture that conversation. “So… How did that go?” she asked.

“Kim, she was trying to set me up with her nephew!” Hailey replied and Kim just started laughing. Suddenly there was a knock on the break room door. Kim walked over to open it and behold, Trudy was standing there, looking annoyed.

“Ladies, do I need to remind you that those vents carry conversations.” She said while pointing at the wall.

Hailey and Kim just stood there speechless, and finally responded in unison, “Sorry, Sarge.” Trudy just huffed and stomped back down the stairs to her desk.

* * *

When Hailey and Kim came out of the breakroom. The guys were staring at them.

Adam asked, “What did you do to Trudy? Like what damage control is needed? I do not want to work any patrols shifts coming up." Jay and Kevin stood next to him nodding in agreeance.

Kim and Hailey looked at each other and Kim responded to the guys, “It’s a girl thing. Don’t worry about it?”

“Don’t worry, you gals know when Trudy is not happy, all of the 21st District is not happy. That's no bueno,” Kevin replied before Adam could say anymore. Hailey looked nervous and was quiet. Jay has been watching Hailey this whole time trying to read her.

“Hailey, what happened?” Jay asked.

Hailey quietly responded back, “Trudy was trying to set me up with her nephew for the Christmas party.”

Jay looked shocked and Adam replied, “Wait, what? You are going to have to repeat that a bit louder, I don’t think I heard that correctly.”

Hailey glared at him, “You heard me. I may have laughed slightly at her downstairs due to a dancing moves comment and then she heard me up here talking to Kim. “Those, damn, vents.” She mumbled.

Adam walked over to Hailey and put his hand on her shoulder, “Hm, well I think the only way you're going to be able to fix this is actually going on that date.” Kevin standing back nodded, “Sorry Hailey, I’m going to have to agree with Adam here. You're going to have to take one for the team.”

“Absolutely not!” She said loudly and then quickly quieted down and finished, to avoid another Trudy sighting, “I am not going on a date with her nephew…” Hailey, the whole time, tried to avoid looking at Jay.

“What it’s not like you had an actual date to the party, Hailey. Just do it.” Adam replied.

“Now, just because she does not have a date, does not give you guys the right to tell her what she has to do.” Kim replied trying to help Hailey out.

All of the sudden they heard a loud bang and heard Trudy yelling at some patrolman downstairs. Kim looked back at Hailey, “I love you girl, but I cannot deal with that the rest of the week. It’s only Monday.”

Hailey was speechless, she looked at her at the group of co-workers, and just threw her hands up in the air and walked to the locker room. She could not believe they were suggesting the only way to fix this was for her to go on a date with Trudy's nephew. Also, she could not believe that Trudy was taking it so personal, but again Trudy was protective over people she loved. Hailey knew that from many life-death scenarios they had all gone through in her years at the 21st.

“Bro, you need to go talk some sense into your partner.” Kevin told Jay. Jay slowly made his way down the hall following Hailey to the locker room.

* * *

Jay closed the locker room door behind him, and approached Hailey, who was sitting on the bench by her locker. Before he could say anything she noticed him and immediately started talking, “Can you believe them? I am not going on a date with her nephew.” She stood up and was pacing while explaining to Jay.

“Maybe, it’s time we tell them about “us.” He replied quietly. “It would definitely get Trudy off both our backs.” Hailey stopped in her tracks and turned around to face him.

“Wait, that’s why you were late this morning and without coffee? Didn't she have any nieces for you?” She asked.

Jay just shrugged his shoulders and smiled back, “Lucky me?” Hailey playfully swatted her arms at his chest. All of a sudden Jay noticed Hailey's facial expression change. She replied, “If we are going to decide to let them know about “us,” I think we should have some fun messing with them all first.”

“What did you have in mind?” Jay asked very curiously wondering where this was going to go. He definitely did not think it was going to be this easy to convince Hailey to come clean to the group.

“You are going to tell the group out there,” pointing out to the hall, “That, I went to talk to Sarge to fix it. We are all good.” Jay listened and asked, “What are you going to tell Sarge?”

“A really good friend reached out and now I have a date for the Christmas work party. So, I can’t go with her nephew, and apologize.” She shrugged her shoulders, making it sound so simple.

“Oh, a really good friend, huh? Jay said teasingly, “Does he happen to have a name?”

“I will call him, Jacob.” She slipped her arms around his waist and looked up and smiled at him.

“Think we can pull it off?” She asked. “I do.” He kissed her quickly before someone walked in, they separated and went off to handle their tasks individually. They had managed to pull off their little white lie that day. Hailey definitely did have a date, and no his name was not Jacob. It was Jay.

* * *

It was finally the night of the work party. Hailey and Jay decided to show up a little late, so that everyone would be there before they arrived.

At the party, the group of them were all talking. Trudy said, “So, apparently Upton has a date tonight?” The rest of the group looked at Trudy smiling. Kim replied, “I cannot wait to meet your nephew!” Trudy had just grabbed an appetizer of the plate from the waitress and dropped it on the floor. “Damn it, Burgess, my snack! Also, what do you mean my nephew? She isn’t coming with my nephew.”

The group all exclaimed, “Wait, what? Jay said, she was going down to talk to you and make things right." Kim commented.

“Goldilocks told me she has a date with a good friend named Jacob”, Trudy responded.

Kevin responded, “She never mentioned Jacob, did she?" Looking at Adam and Kim.

They responded in unison shaking their heads no.

Trudy was about to say something, then she stopped dead in her tracks staring at the front door. Kim asked, “Sarge, are you ok?”

“Turn around, Burgess. I think we all have been played like a little violin.”

“What are you talking about, Sarge? Kim asked. Trudy grabbed Kim's shoulders and turned her around pointing at the front door.

There stood Jay and Hailey at the front door, holding hands. The two of them saw the reactions from their team. Hailey smirked and just before she turned Jay, to lead him toward the bar, he sent a wink to the group.

“Well, damn we definitely got played.” Adam said.

Right at that moment, Voight walked by looking at the group and back at Jay and Hailey, “Wait, you guys didn’t know? You better start studying for the detective exam now. Because that was way easier to figure out, than any of those questions will ever be."


End file.
